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| Pyridinium chlorochromate Basic information |
| Pyridinium chlorochromate Chemical Properties |
Melting point | 205-208 °C(lit.) | storage temp. | Inert atmosphere,Room Temperature | solubility | Soluble in acetone, benzene, dichloromethane, acetonitrile and tetrahydrofuran. | form | Crystalline Powder | color | Orange | Sensitive | Moisture Sensitive | Merck | 14,7974 | BRN | 7054643 | Exposure limits | OSHA: Ceiling 0.1 mg/m3 NIOSH: IDLH 15 mg/m3; TWA 0.0002 mg/m3 | Stability: | Stable. May react with easily oxidized materials. Incompatible with reducing agents, combustible material, metals, strong reducing agents. | InChIKey | LEHBURLTIWGHEM-UHFFFAOYSA-N | CAS DataBase Reference | 26299-14-9(CAS DataBase Reference) | EPA Substance Registry System | Pyridinium chlorochromate (26299-14-9) |
| Pyridinium chlorochromate Usage And Synthesis |
Chemical Properties | Pyridinium chlorochromate is orange crystalline powder | Uses | Oxidizing agent in organic synthesis.
PCC is pyridinium chlorochromate; PDC is pyridinium dichromate. Both are used in dichloromethane. | Uses | Pyridinium chlorochromate is usually used to oxidize an allylic methylene group.
Oxidation of primary alcohols to aldehydes
![Oxidation of primary alcohols to aldehydes](https://www.chemicalbook.com/NewsImg/2020-03-03/20203311465819495.jpg)
Pyridinium dichromate (PDC) or pyridinium chlorochromate (PCC) in anhydrous media such as dichloromethane oxidizes primary alcohols to aldehydes while avoiding overoxidation to carboxylic acids. | Uses | Pyridinium chlorochromate is used as an oxidizing agent to convert primary and secondary alcohols to aldehydes and ketones respectively. It is involved in the preparation of cyclohexanone, (-)-pulegone and lactones. It plays an important role in the selective mono-oxidation of xylenes to tolualdehydes and arylhydroxyamines to nitroso compounds. Furthermore, it is utilized as an oxidant for amino acids, L-cystine, aniline, cycloalkanols, vicinal and non-vicinal diols as well as in the Babler oxidation reaction. | Reactions | Pyridinium chlorochromate (PCC) is a widespread used oxidation reagent but lacks of selectivity with unsaturated compounds. Furthermore, the workup procedure is quite tedious. Absorption of PCC onto silica gel improves the oxidation but then a reagent excess is necessary to reach appropriate rates. These drawbacks can be overcome by sonication leading to short reaction times and only an small excess of 1.2.-1.5 eq. of PCC is required. Using this reagent has been used to oxidise borneol to camphor in 85% yield.
![Pyridinium chlorochromate Reaction](https://www.chemicalbook.com/NewsImg/2020-02-14/202021421155511714.jpg) | Purification Methods | Dry it in a vacuum for 1hour. It is not hygroscopic and can be stored for extended periods at room temperature without change. If the purity is very suspect, it can be readily prepared. [Corey & Scuggs Tetrahedron Lett 2647 1975, Piancatelli et al. Synthesis 245 1982.] (Possible CARCINOGEN.) § Available commercially on a polymer support. |
| Pyridinium chlorochromate Preparation Products And Raw materials |
Preparation Products | 3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE-->1,3-DIMETHYL-1H-PYRAZOLE-5-CARBALDEHYDE-->Tetrahydropyran-4-carbaldehyde-->3-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBALDEHYDE-->1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBALDEHYDE-->Cyclopropanecarboxaldehyde-->3-(2-METHOXY-PHENYL)-PROPIONALDEHYDE-->1-(2,6-DIFLUOROPYRIDIN-3-YL)PROPAN-1-ONE-->2-(4-Methylpiperazin-1-yl)-6-(trifluoromethyl)pyrimidine-4-carbaldehyde-->5-CHLORO INDAZOLE-3-CARBOXALDEHYDE-->3-(4-NITRO-PHENYL)-PROPIONALDEHYDE-->4-(MORPHOLIN-4-YLMETHYL)-1,3-THIAZOL-2-AMINE-->1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde-->3-(2,6-DICHLOROPHENYL)-5-METHYLISOXAZOLE-4-CARBALDEHYDE-->2,5-DIBROMONICOTINALDEHYDE-->TERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE-->TERT-BUTYL 4-(5-FORMYL-4-METHYL-1,3-THIAZOL-2-YL)PIPERIDINE-1-CARBOXYLATE-->,5-Dihydro-5-methyl-6-[4-(4-oxo-1(4H)-pyridinyl)phenyl]-1,2,4-triazin-3(2H)-one-->2-PHENYL-1,3-THIAZOLE-4-CARBALDEHYDE-->TERT-BUTYL 4-(5-FORMYLPYRID-2-YL)PIPERAZINE-1-CARBOXYLATE-->2,4-DIPHENYL-1,3-THIAZOLE-5-CARBALDEHYDE-->N-BOC-L-Prolinal-->2-[4-(TRIFLUOROMETHYL)PHENYL]-1,3-THIAZOLE-4-CARBALDEHYDE-->4-METHYL-2-[4-(TRIFLUOROMETHYL)PHENYL]-1,3-THIAZOLE-5-CARBALDEHYDE |
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